Winter Vacations from $714

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The Latest Winter vacation packages

Price found within the past 48 hours. Click for updated prices.
Magnuson Hotel Ironwood

Magnuson Hotel Ironwood

2 out of 5
Price was $771, price is now $714 per person
$714
per person
Feb 19 - Feb 23
found 2 hours ago
Roundtrip flight included
Kalamazoo (AZO) to Ironwood (IWD)
6/10 (283 reviews)
Staff and Kiosk was Great. Same guy from the Philippines 2 times in a row. Everything is good

Reviewed on Jan 7, 2026

Davos Chalet

Davos Chalet

2 out of 5
Price was $934, price is now $837 per person
$837
per person
Feb 19 - Feb 23
found 2 hours ago
Roundtrip flight included
Kalamazoo (AZO) to Ironwood (IWD)
8.8/10 Excellent! (94 reviews)
It was such a beauitful place to stay especially with the fall colors. There were community snacks including s’mores which was such a great surprise!

Reviewed on Oct 22, 2025

Days Inn by Wyndham Hurley

Days Inn by Wyndham Hurley

2 out of 5
Price was $1,147, price is now $1,050 per person
$1,050
per person
Feb 19 - Feb 23
found 2 hours ago
Roundtrip flight included
Kalamazoo (AZO) to Ironwood (IWD)
8.4/10 Very Good! (892 reviews)
Was a good place to stay, last time we were in however the hottub was out of order and they did not inform us of this before check-in. That was really the only disappointment. Breakfasts were excellent for a Hotel style free breakfast. Room was clean and our stay was quiet.

Reviewed on Oct 20, 2025

AmericInn by Wyndham Silver City

AmericInn by Wyndham Silver City

2.5 out of 5
Price was $1,021, price is now $938 per person
$938
per person
Feb 19 - Feb 23
found 2 hours ago
Roundtrip flight included
Kalamazoo (AZO) to Ironwood (IWD)
9/10 Wonderful! (1,001 reviews)
When you walked into the first doors there was dog poop that someone kept covering up with a rug instead of actually cleaning up, it was there for 2 days! The lady at the bar was very rude when I asked about mixed drinks as I am not a drinker and just wanted something that tasted good after my day of riding out on the trails. The pool felt dirty, I got out and when I rubbed my leg it felt like dead skin/dirt. The gym could definitely use some more equipment.

Reviewed on Dec 31, 2025

Indianhead Ironwood Motel

Indianhead Ironwood Motel

2.5 out of 5
Price was $780, price is now $722 per person
$722
per person
Feb 19 - Feb 23
found 2 hours ago
Roundtrip flight included
Kalamazoo (AZO) to Ironwood (IWD)
7.8/10 Good! (275 reviews)
Check in was easy, staff was great and will becoming back to this hotel everytime I go to ironwood!!!

Reviewed on Dec 10, 2025

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Winter Hotel Deals

Great 4 Season Family Getaway! Quiet, yet full of Fun!

Great 4 Season Family Getaway! Quiet, yet full of Fun!

Winter WI
9.6/10 Exceptional! (76 reviews)
There where a few things we would change but overall a great stay and the view is amazing.. the host is amazing at getting back to us quickly!

Reviewed on Sep 22, 2025

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Great 4 Season Family Getaway! Quiet, yet full of Fun!
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

Winter, Wisconsin WI
10/10 Exceptional! (34 reviews)
The cabin exceeded our expectations in every way. From the cozy heated floors and the inviting fireplace to the fully stocked kitchen, every detail was thoughtfully designed for comfort and convenience. The hot tub was spotless and perfectly hot, offering a relaxing retreat. And the endless supply ...

Reviewed on Nov 3, 2025

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Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
Rustic Cabin on Private Lake

Rustic Cabin on Private Lake

Winter WI
9.2/10 Wonderful! (5 reviews)
Very comfortable and clean. Well stocked. Loons and deer frequent sightings. Easy to communicate with host.

Reviewed on Jul 19, 2025

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Rustic Cabin on Private Lake
See all 672 properties in Winter
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Winter Vacation Packages

Winter Essential Information

Language
English
Currency
U.S dollars
Population
310

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Frequently asked questions

How much does a Winter vacation package cost?
You can pick up a vacation package to this popular destination from $714 on Expedia. But how much your vacation to Winter costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winter?
February, September and November are the best times to search for cheap Winter vacation packages. Traveling in less busy months means you'll typically find reduced prices on hotels and flights.
How many days is enough for Winter?
With a well-planned itinerary, you can easily hit the main Winter sights in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Winter vacation for longer.
How to find the best Winter package deals?
Bagging a cheap Winter package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Winter package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winter vacation as a package?
You can enjoy significant savings on your Winter escape by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winter?
If you've got your Winter travel dates locked in, book early to score some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Winter vacation packages?
Jet off on your dream trip to Winter with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait for your next paycheck — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.